3-Hydroxy-4-{[(4-fluorophenyl)imino]methyl}phenyl Octadecanoate
1
Department of Chemical Science, Faculty of Science, Universiti Tunku Abdul Rahman, Jln Universiti, Bandar Barat, 31900 Kampar, Perak, Malaysia
2
Department of Science, Faculty of Engineering and Science, Universiti Tunku Abdul Rahman, Jln Genting Jelang, Setapak, 53300 Kuala Lumpur, Malaysia
*
Author to whom correspondence should be addressed.
†
Present address: Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543.
Molbank 2010, 2010(2), M673; https://doi.org/10.3390/M673
Submission received: 25 March 2010
/
Accepted: 8 April 2010
/
Published: 9 April 2010
Abstract
:A new Schiff base ester, 3-hydroxy-4-{[(4-fluorophenyl)imino]methyl}phenyl octadecanoate, was synthesized and its IR, 1H NMR, 13C NMR and MS spectroscopic data are presented.
Schiff base (CH=N) compounds have received a considerable amount of attention from many sresearchers owing to their importance in exhibiting thermochromism and photochromism [1,2,3]. Aromatic Schiff bases possessing a long alkyl chain have received overwhelming attention due to their possibility to show liquid crystallinity properties such as smectic and nematic phases [4,5,6,7].
Synthesis
4-Formyl-3-hydroxyphenyl octadecanoate was previously prepared via Steglich esterification [8]. In a round-bottom flask, a mixture of the aldehyde I (1.74 g, 5.0 mmol), 4-fluoroaniline (0.56 g, 5.0 mmol) and absolute ethanol (40 mL) was refluxed for 3 h with stirring. The reaction mixture was filtered and the solvent was removed from the filtrate by evaporation. Recrystallization from absolute ethanol gave the title compound as a yellow solid (1.84 g, 74%).
Melting point: 95.4 °C
MS (EI): m/z = 497 (M+)
IR (KBr, cm−1): 3454 (O-H), 2954, 2918, 2849 (C-H aliphatic); 1758 (C=O ester); 1624 (C=N); 1609, 1510 (C=C aromatic), 1245 (C-F).
1H NMR (400 MHz, CDCl3): δ/ppm 0.89 (t, 3H, J = 7.0 Hz, CH3), 1.28-1.45 {m, 28H, CH3(CH2)14-}, 1.74 (quint, 2H, J = 7.3 Hz, -CH2CH2COO-), 2.56 (t, 2H, J = 7.5 Hz, -CH2COO-), 6.71 (dd, 1H, J = 2.2, 8.4 Hz, Ar-H), 6.78 (d, 1H, J = 2.2 Hz, Ar-H), 7.10 (m, 2H, Ar-H), 7.25 (m, 2H, Ar-H), 7.38 (d, 1H, J = 8.4 Hz, Ar-H), 8.58 (s, 1H, CH=N), 13.39 (s, 1H, OH).
13C NMR (100 MHz, CDCl3): δ/ppm 172.1 (COO), 162.8 (CH=N), 161.9, 160.9, 155.0, 144.8, 133.5, 123.0, 117.4, 116.7, 113.3, 110.8 (aromatic carbons), 34.8 (-CH2COO-), 25.3 (-CH2CH2COO-), 32.3, 30.1, 30.0, 29.9, 29.8, 29.7, 29.6, 29.5, 23.1 (CH3(CH2)14-), 14.5 (CH3).
Elemental analysis: Calculated for C31H44FNO3 C, 74.81%, H, 8.91%, N, 2.81%; Found: C, 74.92%, H, 8.98%, N, 2.70%.
Supplementary materials
Supplementary File 1Supplementary File 2Supplementary File 3Acknowledgements
The author (S.T. Ha) would like to thank Universiti Tunku Abdul Rahman for the financial support and research facilities.
References and Notes
- Hadjoudis, E.; Vittorakis, M.; Moustakali-Mavridis, I. Photochromism and thermochromism of schiff bases in the solid state and in rigid glasses. Tetrahedron 1987, 43, 1345–1360. [Google Scholar] [CrossRef]
- Hadjoudis, E.; Rontoyianni, A.; Ambroziak, K.; Dziembowska, T.; Mavridis, I.M. Photochromism and thermochromism of solid trans-N,N'-bis(salicylidene)-1,2-cyclohexanediamines and trans-N,N'-bis-(2-hydroxynaphylidene)-1,2-cyclohexanediamine. J. Photochem. Photobiol. A - Chem. 2004, 162, 521–530. [Google Scholar] [CrossRef]
- Oshima, A.; Momotake, A.; Arai, T. Photochromism, thermochromism, and solvatochromism of naphthalene-based analogues of salicylideneaniline in solution. J. Photochem. Photobiol. A - Chem. 2004, 162, 473–479. [Google Scholar] [CrossRef]
- Yeap, G.Y.; Ha, S.T.; Lim, P.L.; Boey, P.L.; Ito, M.M.; Sanehisa, S.; Youhei, Y. Synthesis, physical and mesomorphic properties of Schiff’s base esters containing ortho-, meta- and para-substituents in benzylidene-4’-alkanoyloxyanilines. Liq. Cryst. 2006, 33, 205–211. [Google Scholar] [CrossRef]
- Ha, S.T.; Ong, L.K.; Wong, J.P.W.; Yeap, G.Y.; Lin, H.C.; Ong, S.T.; Koh, T.M. Mesogenic Schiff’s base ether with dimethylamino end group. Phase Transit. 2009, 82, 387–397. [Google Scholar] [CrossRef]
- Ha, S.T.; Ong, L.K.; Ong, S.T.; Yeap, G.Y.; Wong, J.P.W.; Koh, T.M.; Lin, H.C. Synthesis and mesomorphic properties of new Schiff base esters with different alkyl chains. Chin. Chem. Lett. 2009, 20, 767–770. [Google Scholar] [CrossRef]
- Ha, S.T.; Ong, L.K.; Yasodha, S.; Yeap, G.Y.; Boey, P.L.; Lin, H.C. New mesogenic Schiff base esters with polar chloro substituent: synthesis, thermotropic properties and X-ray diffraction studies. Am. J. Appl. Sci. 2010, 7, 214–220. [Google Scholar] [CrossRef]
- Ha, S.T.; Ong, S.T.; Chong, Y.T.; Yeap, G.Y. Synthesis of 4-{[(3-chlorophenyl)imino]methyl}-3-hydroxyphenyl myristate. Molbank 2009, 2009, M629. [Google Scholar] [CrossRef]
© 2010 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland. This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
Share and Cite
MDPI and ACS Style
Ha, S.-T.; Ng, M.-Y.; Koh, T.-M.; Lee, T.-L. 3-Hydroxy-4-{[(4-fluorophenyl)imino]methyl}phenyl Octadecanoate. Molbank 2010, 2010, M673. https://doi.org/10.3390/M673
AMA Style
Ha S-T, Ng M-Y, Koh T-M, Lee T-L. 3-Hydroxy-4-{[(4-fluorophenyl)imino]methyl}phenyl Octadecanoate. Molbank. 2010; 2010(2):M673. https://doi.org/10.3390/M673
Chicago/Turabian StyleHa, Sie-Tiong, Mei-Yoke Ng, Teck-Ming Koh, and Teck-Leong Lee. 2010. "3-Hydroxy-4-{[(4-fluorophenyl)imino]methyl}phenyl Octadecanoate" Molbank 2010, no. 2: M673. https://doi.org/10.3390/M673
Note that from the first issue of 2016, this journal uses article numbers instead of page numbers. See further details here.
Display in JSmol Viewer
